Hotel for the Thirties Crowd

Question

I like Cheeca or Islander Resort for myself, but I need to recommend a place to a younger (early 30s) group of 5 people staying one nite on their way to Key West. They would want the liveliest party hotel, although the Islamorada hotels & resorts may all be pretty quiet compared to Miami, Key West etc.?

Where would be the liveliest of the bunch?

There used to be a party place called the Postcard Inn if I recall correctly, but I'm not familiar with the property that replaced it?

And is there still a free shuttle that can handle a group of five for tips, or should they plan to use uber XL, or taxi?

Thanks!

Answer

Islamorada is known for being more laid-back compared to Key West or Miami, so “party hotels” in the traditional sense are limited. Most resorts cater to couples or families and focus on relaxing, waterfront activities. However, there are a few options that tend to attract a younger crowd looking for a lively atmosphere.

For a group in their early 30s staying one night on the way to Key West, here are some of the liveliest options in Islamorada:

The Islander Resort – Known for its casual, fun vibe with tiki bars and waterfront views. While it’s not a “club” atmosphere, it does host live music on certain nights and has poolside social areas where guests mingle.
Cheeca Lodge & Spa – More upscale and relaxing, but can be lively around the pool area or during occasional events. Not ideal for a full-on party vibe, but great for socializing with other guests.
Postcard Inn (now part of Holiday Inn Resort Islamorada) – This property has changed over the years but retains a younger, energetic feel with outdoor bars, water sports rentals, and casual dining. It’s arguably the closest to a “party” scene in Islamorada, especially for groups who want to hang out by the pool or dock.

Transportation and group logistics:

Most resorts in Islamorada do not offer free shuttles for offsite excursions or bars, so for a group of five, Uber XL or local taxis are your best bet for getting around safely, especially if planning to enjoy drinks.
Many guests rent bicycles or scooters if staying locally, but given the distances between nightlife spots and resorts, ride-sharing is more practical for a one-night stay.
Tip: Plan to stay onsite for evening activities, as the nightlife options in Islamorada are relatively limited and spread out compared to Key West.

In summary, the Postcard Inn/ Holiday Inn Resort Islamorada is probably the best bet for a lively one-night stop, with The Islander Resort as a close second if the group prefers a slightly more social yet relaxed atmosphere. Offsite travel will require Uber XL or taxis rather than a free shuttle.

Hotel for the Thirties Crowd

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